Synthesis and applications of (1R, 5S,6S)-6-(2,2-dimethylpropanamido)spiro[4.4]nonan-1-ol as a chiral auxiliary in Diels-Alder reactions

Authors
Burke, MJ Allan, MM Parvez, M Keay, BA
Citation
Mj. Burke et al., Synthesis and applications of (1R, 5S,6S)-6-(2,2-dimethylpropanamido)spiro[4.4]nonan-1-ol as a chiral auxiliary in Diels-Alder reactions, TETRAHEDR-A, 11(13), 2000, pp. 2733-2739
Citations number
35
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
11
Issue
13
Year of publication
2000
Pages
2733 - 2739
Database
ISI
SICI code
0957-4166(20000714)11:13<2733:SAAO(5>2.0.ZU;2-3
Abstract
A short asymmetric synthesis of (1R,5S,6S)-6-(2,2-dimethylpropanamido)spiro [4.4]nonan-1-ol 7 is described along with its application as a chiral auxil iary in various Diels-Alder reactions. The enantioselectivity of the Diels- Alder adducts ranged from 86-98% ee. The Diels-Alder adducts were easily re moved from the chiral auxiliary and the latter was recyclized. The absolute and relative stereochemistry of 7 was determined from an X-ray crystal str ucture of the p-bromobenzoate derivative of 7. (C) 2000 Elsevier Science Lt d. All rights reserved.